Ammonium Chloride → Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-(1-hydroxyethyl)-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

HRID 17088

反応式

HRID 17088 の反応式
[CH3:1][Mg]Br.[F:4][C:5]([F:44])([F:43])[C:6]1[CH:7]=[C:8]([CH:36]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:38]=1)[CH2:9][N:10]([CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[C:26]1[CH:31]=[C:30]([CH:32]=[O:33])[CH:29]=[CH:28][C:27]=1[O:34][CH3:35])[C:11](=[O:14])[O:12][CH3:13].[Cl-].[NH4+]>O1CCCC1>[F:4][C:5]([F:43])([F:44])[C:6]1[CH:7]=[C:8]([CH:36]=[C:37]([C:39]([F:40])([F:42])[F:41])[CH:38]=1)[CH2:9][N:10]([CH2:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1[C:26]1[CH:31]=[C:30]([CH:32]([OH:33])[CH3:1])[CH:29]=[CH:28][C:27]=1[O:34][CH3:35])[C:11](=[O:14])[O:12][CH3:13]

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 11699919Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-formyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamateHCID 178418573HCID 178418573、化合物

生成物 1

HCID 11599738Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-(1-hydroxyethyl)-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methylmagnesium bromide (0.59 mL, 0.83 mmol) was added dropwise to a solution of methyl [3,5-bis(trifluoromethyl)benzyl]{[5′-formyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate (Example 73, 289 mg, 0.49 mmol) in anhydrous tetrahydrofuran at 0° C. The solution was allowed to warm to room temperature. Once the reaction was complete, saturated ammonium chloride solution was added to quench the reaction. The mixture was extracted with methylene chloride, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The title compound was obtained by flash chromatography using 30% acetone/hexane. 1H NMR (CDCl3, 600 MHz) δ 7.73 (s, 1H), 7.58 (m, 1H), 7.32-7.51 (m, 5H), 7.11 (m, 1H), 6.94 (m, 1H), 4.87 (m, 1H), 4.25-4.43 (m, 4H), 3.69 (m, 6H), 1.48 (d, J=4.2 Hz, 3H). LC-MS (M+Na) 632.0 (4.18 min).

後処理

  1. customto quench
  2. customthe reaction
  3. extractionThe mixture was extracted with methylene chloride
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-cbb43fe36a5f4822a94b3750e9f2f484
出典データセット
uspto-grants-2010_06
特許番号
US07737295B2

関連ノート

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